Canagliflozin hemihydrate
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MedKoo CAT#: 329456

CAS#: 928672-86-0 (hemihydrate)

Description: Canagliflozin, also known as JNJ-28431754 and TA 7284, is a drug of the gliflozin class or subtype 2 sodium-glucose transport (SGLT-2) inhibitors used for the treatment of type 2 diabetes. SGLT2 is responsible for at least 90% of renal glucose reabsorption (SGLT1 being responsible for the remaining 10%). Blocking this transporter causes up to 119 grams of blood glucose per day to be eliminated through the urine, corresponding to 476 kilocalories. Additional water is eliminated by osmotic diuresis, resulting in a lowering of blood pressure.


Chemical Structure

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Canagliflozin hemihydrate
CAS# 928672-86-0 (hemihydrate)

Theoretical Analysis

MedKoo Cat#: 329456
Name: Canagliflozin hemihydrate
CAS#: 928672-86-0 (hemihydrate)
Chemical Formula: C48H52F2O11S2
Exact Mass:
Molecular Weight: 907.0498
Elemental Analysis: C, 63.56; H, 5.78; F, 4.19; O, 19.40; S, 7.07

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100.0g USD 3650.0 Same day
200.0g USD 4750.0 2 Weeks
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Related CAS #: 928672-86-0 (hemihydrate)   842133-18-0 (free)    

Synonym: JNJ 28431754; JNJ-28431754; JNJ28431754; TA 7284; TA-7284; TA7284; JNJ-24831754-ZAE; JNJ-28431754-AAA; Canagliflozin hemihydrate; brand name: Invokana. Sulisent.

IUPAC/Chemical Name: (3R,4R,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol hemihydrate

InChi Key: VHOFTEAWFCUTOS-HTDYLQHCSA-N

InChi Code: InChI=1S/2C24H25FO5S.H2O/c2*1-13-2-3-15(24-23(29)22(28)21(27)19(12-26)30-24)10-16(13)11-18-8-9-20(31-18)14-4-6-17(25)7-5-14;/h2*2-10,19,21-24,26-29H,11-12H2,1H3;1H2/t2*19-,21-,22+,23-,24?;/m11./s1

SMILES Code: O[C@H]1C(O[C@@H]([C@H]([C@@H]1O)O)CO)C2=CC=C(C(CC3=CC=C(S3)C4=CC=C(C=C4)F)=C2)C.[H]O[H].O[C@H]5C(O[C@@H]([C@H]([C@@H]5O)O)CO)C6=CC=C(C(CC7=CC=C(S7)C8=CC=C(C=C8)F)=C6)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Canagliflozin hemihydrate (JNJ28431754 hemihydrate) is a selective SGLT2 inhibitor
In vitro activity: To understand the mechanism of Cana (Canagliflozin) regulated Abcg5 and Abcg8 expression, this study explored the signaling pathway. Cana has been reported to activate AMPK in several cell lines. In hepG2 cells, Cana could directly activate AMPK and its downstream phosphorylation of ACC (Figure 4B). In Caco2 cells, AMPK was also activated by Cana treatment (Figure 4C). To confirm whether Cana regulated Abcg5 and Abcg8 was AMPK dependent, this study treated hepG2 and Caco2 cells with compound C, a pharmacological inhibitor of AMPK. Inhibition of AMPK pathway abolished Cana increased expression of Abcg5 and Abcg8 in both hepG2 and Caco2 cells (Figure 5A–F, Supplementary Figure 6A–F). Cana upregulated expressions of LXR in both hepG2 and Caco2 cells were also inhibited by Compound C (Supplementary Figure 6G and H). Taken together, Cana increased Abcg5 and Abcg8 expression via activating AMPK pathway. Reference: Drug Des Devel Ther. 2021 May 18;15:2117-2128. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8140894/
In vivo activity: In this study, CAN (Canagliflozin) significantly improved acute lung injures induced by LPS (increased lung edema and lung capillary penetration) in mice. The pathological slice results also indicated this improvement. Immunohistochemistry analysis further indicated that CAN attenuated macrophage (identified by CD11b antibody) infiltration in lung tissues induced by LPS, which may be associated with the decreased chemotactic cytokines, for example, MCP-1 and MIP-2 in lung tissues of mice. In blood samples, CAN significantly reduced the inflammatory factors, which suggested that CAN had a systematic inhibition on immune cell activation in vivo after acute treatment. Although this study used CAN or DXM (Dexamethasone) only for 3 days, more COVID-19 patients may require longer administration of these anti-inflammatory drugs and a safety concern could be considered. In a preliminary experiment, chronic administration (about 3 months) of CAN (25 mg/kg) did not affect the spleen weight in mice compared with untreated controls, whereas 1-month administration of dexamethasone (2 mg/kg) significantly lowered the spleen weight in mice (supplemental Fig. 1) compared with untreated controls. These results indicated that CAN might not significantly affect immune organ development similar to glucocorticoids if patients required a long-term administration. Reference: Int Immunopharmacol. 2021 Jul; 96: 107773. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8106881/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 110.25
Ethanol 100.0 110.25

Preparing Stock Solutions

The following data is based on the product molecular weight 907.0498 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zhao Y, Li Y, Liu Q, Tang Q, Zhang Z, Zhang J, Huang C, Huang H, Zhang G, Zhou J, Yan J, Xia Y, Zhang Z, He J. Canagliflozin Facilitates Reverse Cholesterol Transport Through Activation of AMPK/ABC Transporter Pathway. Drug Des Devel Ther. 2021 May 18;15:2117-2128. doi: 10.2147/DDDT.S306367. PMID: 34040350; PMCID: PMC8140894. 2. Papadopoli D, Uchenunu O, Palia R, Chekkal N, Hulea L, Topisirovic I, Pollak M, St-Pierre J. Perturbations of cancer cell metabolism by the antidiabetic drug canagliflozin. Neoplasia. 2021 Apr;23(4):391-399. doi: 10.1016/j.neo.2021.02.003. Epub 2021 Mar 27. PMID: 33784591; PMCID: PMC8027095. 3. Niu Y, Chen Y, Sun P, Wang Y, Luo J, Ding Y, Xie W. Intragastric and atomized administration of canagliflozin inhibit inflammatory cytokine storm in lipopolysaccharide-treated sepsis in mice: A potential COVID-19 treatment. Int Immunopharmacol. 2021 May 9;96:107773. doi: 10.1016/j.intimp.2021.107773. Epub ahead of print. PMID: 34020392; PMCID: PMC8106881. 4. Nishinarita R, Niwano S, Niwano H, Nakamura H, Saito D, Sato T, Matsuura G, Arakawa Y, Kobayashi S, Shirakawa Y, Horiguchi A, Ishizue N, Igarashi T, Yoshizawa T, Oikawa J, Hara Y, Katsumura T, Kishihara J, Satoh A, Fukaya H, Sakagami H, Ako J. Canagliflozin Suppresses Atrial Remodeling in a Canine Atrial Fibrillation Model. J Am Heart Assoc. 2021 Jan 19;10(2):e017483. doi: 10.1161/JAHA.119.017483. Epub 2021 Jan 5. PMID: 33399004; PMCID: PMC7955321.
In vitro protocol: 1. Zhao Y, Li Y, Liu Q, Tang Q, Zhang Z, Zhang J, Huang C, Huang H, Zhang G, Zhou J, Yan J, Xia Y, Zhang Z, He J. Canagliflozin Facilitates Reverse Cholesterol Transport Through Activation of AMPK/ABC Transporter Pathway. Drug Des Devel Ther. 2021 May 18;15:2117-2128. doi: 10.2147/DDDT.S306367. PMID: 34040350; PMCID: PMC8140894. 2. Papadopoli D, Uchenunu O, Palia R, Chekkal N, Hulea L, Topisirovic I, Pollak M, St-Pierre J. Perturbations of cancer cell metabolism by the antidiabetic drug canagliflozin. Neoplasia. 2021 Apr;23(4):391-399. doi: 10.1016/j.neo.2021.02.003. Epub 2021 Mar 27. PMID: 33784591; PMCID: PMC8027095.
In vivo protocol: 1. Niu Y, Chen Y, Sun P, Wang Y, Luo J, Ding Y, Xie W. Intragastric and atomized administration of canagliflozin inhibit inflammatory cytokine storm in lipopolysaccharide-treated sepsis in mice: A potential COVID-19 treatment. Int Immunopharmacol. 2021 May 9;96:107773. doi: 10.1016/j.intimp.2021.107773. Epub ahead of print. PMID: 34020392; PMCID: PMC8106881. 2. Nishinarita R, Niwano S, Niwano H, Nakamura H, Saito D, Sato T, Matsuura G, Arakawa Y, Kobayashi S, Shirakawa Y, Horiguchi A, Ishizue N, Igarashi T, Yoshizawa T, Oikawa J, Hara Y, Katsumura T, Kishihara J, Satoh A, Fukaya H, Sakagami H, Ako J. Canagliflozin Suppresses Atrial Remodeling in a Canine Atrial Fibrillation Model. J Am Heart Assoc. 2021 Jan 19;10(2):e017483. doi: 10.1161/JAHA.119.017483. Epub 2021 Jan 5. PMID: 33399004; PMCID: PMC7955321.

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1: Davidson JA, Sloan L. Fixed-Dose Combination of Canagliflozin and Metformin for the Treatment of Type 2 Diabetes: An Overview. Adv Ther. 2016 Nov 16. [Epub ahead of print] Review. PubMed PMID: 27854055.

2: Qiu R, Balis D, Capuano G, Xie J, Meininger G. Canagliflozin: Efficacy and Safety in Combination with Metformin Alone or with Other Antihyperglycemic Agents in Type 2 Diabetes. Diabetes Ther. 2016 Oct 12. [Epub ahead of print] Review. PubMed PMID: 27734320.

3: Canagliflozin (Invokana) for Type 2 Diabetes Mellitus [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 Sep. Available from http://www.ncbi.nlm.nih.gov/books/NBK349575/ PubMed PMID: 26962611.

4: Kaur K, Likar N, Dang A, Kaur G. Efficacy and safety of canagliflozin among patients with type 2 diabetes mellitus: A systematic review and meta-analysis. Indian J Endocrinol Metab. 2015 Nov-Dec;19(6):705-21. doi: 10.4103/2230-8210.167562. Review. PubMed PMID: 26693420; PubMed Central PMCID: PMC4673798.

5: Parveen R, Agarwal NB, Kaushal N, Mali G, Raisuddin S. Efficacy and safety of canagliflozin in type 2 diabetes mellitus: systematic review of randomized controlled trials. Expert Opin Pharmacother. 2016;17(1):105-15. doi: 10.1517/14656566.2016.1109629. Review. PubMed PMID: 26650511.

6: Seufert J. SGLT2 inhibitors - an insulin-independent therapeutic approach for treatment of type 2 diabetes: focus on canagliflozin. Diabetes Metab Syndr Obes. 2015 Nov 9;8:543-54. doi: 10.2147/DMSO.S90662. Review. PubMed PMID: 26609242; PubMed Central PMCID: PMC4644173.

7: Syed SH, Gosavi S, Shami W, Bustamante M, Farah Z, Teleb M, Abbas A, Said S, Mukherjee D. A Review of Sodium Glucose Co-transporter 2 Inhibitors Canagliflozin, Dapagliflozin and Empagliflozin. Cardiovasc Hematol Agents Med Chem. 2015;13(2):105-12. Review. PubMed PMID: 26549321.

8: Triplitt C, Cornell S. Canagliflozin Treatment in Patients with Type 2 Diabetes Mellitus. Clin Med Insights Endocrinol Diabetes. 2015 Oct 18;8:73-81. doi: 10.4137/CMED.S31526. Review. PubMed PMID: 26523120; PubMed Central PMCID: PMC4610726.

9: Perkovic V, Jardine M, Vijapurkar U, Meininger G. Renal effects of canagliflozin in type 2 diabetes mellitus. Curr Med Res Opin. 2015 Dec;31(12):2219-31. doi: 10.1185/03007995.2015.1092128. Review. PubMed PMID: 26494163.

10: Rosenthal N, Meininger G, Ways K, Polidori D, Desai M, Qiu R, Alba M, Vercruysse F, Balis D, Shaw W, Edwards R, Bull S, Di Prospero N, Sha S, Rothenberg P, Canovatchel W, Demarest K. Canagliflozin: a sodium glucose co-transporter 2 inhibitor for the treatment of type 2 diabetes mellitus. Ann N Y Acad Sci. 2015 Nov;1358:28-43. doi: 10.1111/nyas.12852. Review. PubMed PMID: 26305874.

11: Fleming JW, Fleming LW, Davis CS. Fixed-dose combinations in type 2 diabetes - role of the canagliflozin metformin combination. Diabetes Metab Syndr Obes. 2015 Jun 25;8:287-94. doi: 10.2147/DMSO.S69282. Review. PubMed PMID: 26150733; PubMed Central PMCID: PMC4485795.

12: Patel S, Gohel K, Patel BG. A Systematic Review on Effect of Canagliflozin in Special Population. Curr Diabetes Rev. 2016;12(3):211-22. Review. PubMed PMID: 26084476.

13: Devineni D, Polidori D. Clinical Pharmacokinetic, Pharmacodynamic, and Drug-Drug Interaction Profile of Canagliflozin, a Sodium-Glucose Co-transporter 2 Inhibitor. Clin Pharmacokinet. 2015 Oct;54(10):1027-41. doi: 10.1007/s40262-015-0285-z. Review. PubMed PMID: 26041408.

14: Scheen AJ. [Canagliflozin (Invokana): kidney SGLT2 cotransporter inhibitor for treating type 2 diabetes]. Rev Med Liege. 2014 Dec;69(12):692-9. Review. French. PubMed PMID: 25796788.

15: Khurana M, Vaidyanathan J, Marathe A, Mehrotra N, Sahajwalla CG, Zineh I, Jain L. Canagliflozin use in patients with renal impairment-Utility of quantitative clinical pharmacology analyses in dose optimization. J Clin Pharmacol. 2015 Jun;55(6):647-56. doi: 10.1002/jcph.466. Review. PubMed PMID: 25612234.

16: Amblee A. Patient profiling in diabetes and role of canagliflozin. Pharmgenomics Pers Med. 2014 Nov 18;7:367-77. doi: 10.2147/52761.S0. Review. PubMed PMID: 25540592; PubMed Central PMCID: PMC4270036.

17: Sehgal V, Bajwa SJ, Sehgal R, Consalvo JA. Management of diabetes in the elderly with canagliflozin: A newer hypoglycemic drug on the horizon. J Pharmacol Pharmacother. 2014 Oct;5(4):227-31. doi: 10.4103/0976-500X.142428. Review. Erratum in: J Pharmacol Pharmacother. 2015 Jan-Mar;6(1):58. PubMed PMID: 25422561; PubMed Central PMCID: PMC4231550.

18: Boyle LD, Wilding JP. A safety evaluation of canagliflozin : a first-in-class treatment for type 2 diabetes. Expert Opin Drug Saf. 2014 Nov;13(11):1535-44. doi: 10.1517/14740338.2014.959488. Review. PubMed PMID: 25340618.

19: Brunton S, Reid TS. Canagliflozin, a sodium glucose co-transporter 2 inhibitor, for the management of type 2 diabetes. Hosp Pract (1995). 2014 Aug;42(3):96-108. doi: 10.3810/hp.2014.08.1122. Review. PubMed PMID: 25255411.

20: Rosiak M, Grzeszczak S, Kosior DA, Postuła M. Emerging treatments in type 2 diabetes: focus on canagliflozin. Ther Clin Risk Manag. 2014 Aug 21;10:683-9. doi: 10.2147/TCRM.S39145. Review. PubMed PMID: 25187722; PubMed Central PMCID: PMC4149387.



Additional Information

Related CAS#
842133-18-0 (Canagliflozin)
928672-86-0 (Canagliflozin hemihydrate)